Strain-release photocatalysis

P Bellotti, F Glorius - Journal of the American Chemical Society, 2023 - ACS Publications
The concept of strain in organic compounds is as old as modern organic chemistry and was
initially introduced to justify the synthetic setbacks along the synthesis of small ring systems …

Three-dimensional saturated C(sp3)-rich bioisosteres for benzene

J Tsien, C Hu, RR Merchant, T Qin - Nature Reviews Chemistry, 2024 - nature.com
Benzenes, the most ubiquitous structural moiety in marketed small-molecule drugs, are
frequently associated with poor 'drug-like'properties, including metabolic instability, and poor …

Intermolecular [2π+2σ]-photocycloaddition enabled by triplet energy transfer

R Kleinmans, T Pinkert, S Dutta, TO Paulisch, H Keum… - Nature, 2022 - nature.com
For more than one century, photochemical [2+ 2]-cycloadditions have been used by
synthetic chemists to make cyclobutanes, four-membered carbon-based rings. In this …

Photochemical intermolecular [3σ+ 2σ]-cycloaddition for the construction of aminobicyclo [3.1. 1] heptanes

Y Zheng, W Huang, RK Dhungana… - Journal of the …, 2022 - ACS Publications
The development of synthetic strategies for the preparation of bioisosteric compounds is a
demanding undertaking in medicinal chemistry. Numerous strategies have been developed …

Synthesis of meta-substituted arene bioisosteres from [3.1.1]propellane

N Frank, J Nugent, BR Shire, HD Pickford, P Rabe… - Nature, 2022 - nature.com
Small-ring cage hydrocarbons are popular bioisosteres (molecular replacements) for
commonly found para-substituted benzene rings in drug design. The utility of these cage …

Synthesis of polysubstituted 2-oxabicyclo [2.1. 1] hexanes via visible-light-induced energy transfer

Y Liang, R Kleinmans, CG Daniliuc… - Journal of the American …, 2022 - ACS Publications
Synthesis of bicyclic scaffolds has attracted growing interest because they are of high
importance in modern pharmaceutical development. Here we report a strategy to access …

A catalytic alkene insertion approach to bicyclo [2.1. 1] hexane bioisosteres

S Agasti, F Beltran, E Pye, N Kaltsoyannis… - Nature Chemistry, 2023 - nature.com
Abstract C (sp 3)-rich bicyclic hydrocarbon scaffolds, as exemplified by bicyclo [1.1. 1]
pentanes, play an increasingly high-profile role as saturated bioisosteres of benzenoids in …

Lewis acid catalyzed formal (3+ 2)‐cycloaddition of bicyclo [1.1. 0] butanes with ketenes

N Radhoff, CG Daniliuc, A Studer - … Chemie International Edition, 2023 - Wiley Online Library
Abstract Design, synthesis and application of benzene bioisosteres have attracted a lot of
attention in the past 20 years. Recently, bicyclo [2.1. 1] hexanes have emerged as highly …

Catalytic formal [2π+ 2σ] cycloaddition of aldehydes with bicyclobutanes: expedient access to polysubstituted 2‐oxabicyclo [2.1. 1] hexanes

Y Liang, F Paulus, CG Daniliuc… - Angewandte Chemie …, 2023 - Wiley Online Library
Synthesis of bicyclic scaffolds has attracted tremendous attention because they are playing
an important role as saturated bioisosteres of benzenoids in modern drug discovery. Here …

2-Oxabicyclo[2.1.1]hexanes as saturated bioisosteres of the ortho-substituted phenyl ring

A Denisenko, P Garbuz, NM Voloshchuk, Y Holota… - Nature Chemistry, 2023 - nature.com
The ortho-substituted phenyl ring is a basic structural element in chemistry. It is found in
more than three hundred drugs and agrochemicals. During the past decade, scientists have …